3* The Willows Hotel

The Guesthouse Hotel is one of GayMapper’s favourite Chicago choices, particularly if you prefer the neighbourhood feel of Andersonville to staying Downtown. Accommodation is apartment-style, with spacious one-, two- and three-bedroom suites featuring full kitchens and living areas, making it especially useful for longer stays or trips with friends. The surrounding Andersonville neighbourhood has restaurants, independent shops and a strong LGBTQ+ presence, with several queer venues within easy reach. You’re well north of the major Downtown sights, but public transport makes them accessible and Northalsted is also straightforward to reach. GayMapper tip: an excellent option if you want space, a genuinely local neighbourhood and easy access to Chicago’s LGBTQ+ life.

Hampton Inn Chicago North-Loyola sits well north of Downtown in Rogers Park, giving you a more neighbourhood-based stay than most of GayMapper’s Chicago choices. It’s particularly useful if you want to explore the northern side of the city rather than spend the whole trip around the Loop. Rooms are modern and straightforward, breakfast is included, and there’s a rooftop terrace with views towards Lake Michigan. Loyola CTA station is just a short walk away, with Red Line trains running south through the city. This isn’t a nightlife-first choice — Northalsted and Andersonville both require a journey — but rates can be attractive compared with more central hotels. GayMapper tip: worth considering for value and transport links rather than proximity to the gay bars.

City Suites has one of the handiest locations in Lakeview, just beside Belmont CTA station and within easy walking distance of the bars around Northalsted. That makes it a particularly convenient base if gay nightlife is going to be a big part of your Chicago trip. The hotel has an older, Art Deco-influenced feel, with comfortable rooms and a more intimate atmosphere than the big Downtown hotels. Wrigley Field is also within walking distance. With Red, Brown and Purple Line trains practically outside, Downtown Chicago is easy to reach when you want to switch from nightlife to sightseeing. GayMapper tip: location is the big selling point here — especially if you want the gay bars close by and excellent public transport.

Majestic Hotel offers a quieter alternative in Lakeview while still keeping you within reasonable reach of Northalsted’s gay bars and clubs. It occupies a residential spot east of Wrigley Field, giving the hotel a more neighbourhood feel than the busier properties around Belmont. The historic building has a cosy, traditional style rather than a sleek contemporary look, and breakfast is included. Lake Michigan and the lakefront are also nearby. You’ll have a little further to walk for the main nightlife than from City Suites or Hawthorne Terrace, but it can be a pleasant compromise if you prefer somewhere calmer. GayMapper tip: best for travellers who want Lakeview convenience without staying right in the middle of the action.

The Hotel at Midtown is a little different from Chicago’s typical city hotels. It forms part of the huge Midtown Athletic Club complex, making the sports, fitness and wellness facilities a major part of the experience. Rooms are modern and stylish, while guests have access to extensive facilities including fitness areas, swimming pools, tennis and spa services. The location between Bucktown and Lincoln Park is less convenient for conventional sightseeing than Downtown, and the main Northalsted gay scene isn’t on the doorstep either. It works particularly well if you like the idea of combining a Chicago city break with serious gym and leisure facilities. GayMapper tip: one to choose for the facilities rather than the location — especially if a good hotel gym means rather more to you than a treadmill in a basement.

The Drake is one of Chicago’s classic grand hotels, occupying a prominent position at the northern end of the Magnificent Mile close to Oak Street Beach and the Gold Coast. Expect traditional rather than cutting-edge luxury, with an imposing historic building, elegant public spaces and a real sense of old-school Chicago. The location is excellent for shopping, restaurants and central sightseeing, with the lakefront just outside. You’ll be well away from the main gay nightlife around Northalsted and Andersonville, so evenings out will involve a taxi, rideshare or public transport. GayMapper tip: choose The Drake for history, atmosphere and a prime central location rather than proximity to Chicago’s gay scene.